Nitric Acid → N-(2-ethyl-6-nitrophenyl)acetamide

HRID 711750

반응식

HRID 711750 반응식
[N+:1]([O-:4])(O)=[O:2].[CH2:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14](=[O:16])[CH3:15])[CH3:6].C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C.C(OC(=O)C)(=O)C.O>[CH2:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:1]([O-:4])=[O:2])[C:8]=1[NH:13][C:14](=[O:16])[CH3:15])[CH3:6]

참가 물질

7

반응물 3

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 36332O-Ethylacetanilide

생성물 1

HCID 14147006N-(2-ethyl-6-nitrophenyl)acetamide수율 48%

시약·촉매·용매 3

HCID 176Acetic Acid용매2회HCID 962Water용매HCID 7918Acetic Anhydride용매

반응 조건

온도
0 °C

실험 절차

A solution of nitric acid (4.2 mL) in glacial acetic acid (5.2 mL)) was added drop wise to solution of N-(2-ethylphenyl)acetamide (Example 139f) (1.00 g, 6.13 mmol) in AcOH (22 mL) and acetic anhydride (18 mL) at 0° C. The reaction was stirred at 0° C. for 1 h, diluted with water (50 mL) and neutralized with Na2CO3 (pH˜8). The neutralized mixture was extracted with EtOAc (3×50 mL), the combined extract was washed with water and brine, and dried with anhydrous MgSO4. The filtrate was evaporated and the residue was purified on HPLC to give 0.62 g (48%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 9.81 (broad s, 1H), 7.68-7.73 (m, 1H), 7.57-7.62 (m, 1H), 7.39 (t, J=8.0 Hz, 1H), 2.64 (q, J=8.0 Hz, 2H), 2.00 (s, 3H), 1.10 (t, J=8.0 Hz, 3H).

후처리

  1. extractionThe neutralized mixture was extracted with EtOAc (3×50 mL)
  2. extractionthe combined extract
  3. washwas washed with water and brine
  4. dry with materialdried with anhydrous MgSO4
  5. customThe filtrate was evaporated
  6. customthe residue was purified on HPLC

출처 및 근거

ORD 기록
ord-91d7654e4ff74aebb135e6dc8a3fecd3
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181276B2

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